Process for synthesis of 5.alpha.-cholest-8(14)-en...

Details Process for synthesis of 5.alpha.-cholest-8(14)-en... Process for synthesis of 5.alpha.-cholest-8(14)-en...

C - Chemistry, Metallurgy

07

J

260/14, 260/60

C07J 9/00 (2006.01) C07J 71/00 (2006.01)

Patent

CA 1287623

ABSTRACT A process for preparing 15-oxygenated sterols, such as 3.beta.-hydroxy-5.alpha.-cholest-8(14)-ene-15 one, comprising coverting 7-dehydrocholesterol to 3.beta.-benzoyloxycholesta-5,7-diene, converting the 3.beta.-benzoyloxycholesta-5,7-diene to a 3.beta.-benzoyloxy-5-cholesta- 7,14-dience, converting the 3.beta.-benzoyloxy-5-cholesta-7,14-diene to a 3.beta.-benzoyloxy-14.alpha.,15.alpha.-epoxy-5-cholest-7-ene and converting the 3.beta.-benzoyloxy-14.alpha.,15.alpha.-epoxy-5-cholest-7-ene to a 15-oxygenated sterol. Preferably, the 3.beta.-benzoyloxy-cholesta-5,7-diene is converted to a 3.beta.-benzoyloxy-5-cholesta-7,14-diene by (i) contacting 3.beta.-benzoyloxy-cholesta-5,7-diene, in a solvent at a temperature of at most about -55°C, with HCl at a concentration of at least about 2.0 M for a time sufficient to convert the 3.beta.-benzoyl-oxycholesta- 5,7-diene to a 3.beta.-benzoyloxy-5-cholesta-7,14-diene; (ii) neutralizing the resultant reaction mixture with a base to prevent formation of a significant amount of 3.beta.-benzoyloxy-5-cholesta-8,14-diene; and (iii) recovering the 3.beta.-benzoyloxy-5-cholesta-7,14-diene. The 15-oxygenated sterols are useful for inhibiting the biosynthesis of mevalonic acid, which in turn results in the reduction of serum cholesterol levels in animals, amongst other effects. -39-

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